Formic Acid → tert-Butyl [(2-chlorophenyl)(phenylsulphonyl)methyl]carbamate

HRID 2402793Notes

Reaction equation

HRID 2402793 reaction equation
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].[Na+].[C:10]1([S:16]([O-:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C(O)=O>CO.O>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 69962-ChlorobenzaldehydeHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 59536806tert-Butyl [(2-chlorophenyl)(phenylsulphonyl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Quantities of 2.78 g (23.7 mmol) of tert-butyl carbamate and 7.79 g (47.4 mmol) of benzenesulphinic acid sodium salt were introduced in 55 ml of methanol/water 1:2 at RT and admixed with 5 g (35.6 mmol) of 2-chlorobenzaldehyde and then with 1.78 ml (47.1 mmol) of formic acid. The mixture was stirred at RT for 2 days. The white solid precipitated was filtered off with suction and washed in succession twice each with water and diethyl ether. Drying in an HV gave 5.77 g (42% of theory) of the title compound.

Workup

  1. customThe white solid precipitated
  2. filtrationwas filtered off with suction
  3. washwashed in succession twice each with water and diethyl ether
  4. customDrying in an HV

Sources & evidence

ORD record
ord-ccd4620d3349413d909ec812aab41c2b
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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